CN1495168A - 制备杀虫剂的中间体 - Google Patents
制备杀虫剂的中间体 Download PDFInfo
- Publication number
- CN1495168A CN1495168A CNA031522416A CN03152241A CN1495168A CN 1495168 A CN1495168 A CN 1495168A CN A031522416 A CNA031522416 A CN A031522416A CN 03152241 A CN03152241 A CN 03152241A CN 1495168 A CN1495168 A CN 1495168A
- Authority
- CN
- China
- Prior art keywords
- formula
- compound
- reaction
- under
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000575 pesticide Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 10
- -1 2,6-dichlor-4-trifluoromethyl phenyl Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 30
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical class N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 6
- 229960000935 dehydrated alcohol Drugs 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical class CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XBVNDLWWXOWJFY-UHFFFAOYSA-N C=O.OC#N Chemical compound C=O.OC#N XBVNDLWWXOWJFY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YMJLEPMVGQBLHL-UHFFFAOYSA-N 1h-pyrazole-5-carbonitrile Chemical compound N#CC1=CC=NN1 YMJLEPMVGQBLHL-UHFFFAOYSA-N 0.000 description 1
- SBGNZVXQHNZLDT-UHFFFAOYSA-N 5-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1h-pyrazole Chemical class ClC1=CC(C(F)(F)F)=CC(Cl)=C1C1=NNC=C1 SBGNZVXQHNZLDT-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- CXDGRSYTPLHQMC-UHFFFAOYSA-N ethyl 2-cyanoacetate;sodium Chemical compound [Na].CCOC(=O)CC#N CXDGRSYTPLHQMC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000012451 post-reaction mixture Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006273 synthetic pesticide Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/16—Preparation of carboxylic acid nitriles by reaction of cyanides with lactones or compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9604691.7A GB9604691D0 (en) | 1996-03-05 | 1996-03-05 | New processes for preparing pesticidal intermediates |
| GB9604691.7 | 1996-03-05 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB971928673A Division CN1137090C (zh) | 1996-03-05 | 1997-03-03 | 制备杀虫剂中间体的新方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1495168A true CN1495168A (zh) | 2004-05-12 |
Family
ID=10789895
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA031522416A Pending CN1495168A (zh) | 1996-03-05 | 1997-03-03 | 制备杀虫剂的中间体 |
| CNB971928673A Expired - Lifetime CN1137090C (zh) | 1996-03-05 | 1997-03-03 | 制备杀虫剂中间体的新方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB971928673A Expired - Lifetime CN1137090C (zh) | 1996-03-05 | 1997-03-03 | 制备杀虫剂中间体的新方法 |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6133432A (enExample) |
| EP (1) | EP0888291B1 (enExample) |
| JP (1) | JP4039693B2 (enExample) |
| KR (1) | KR100530974B1 (enExample) |
| CN (2) | CN1495168A (enExample) |
| AR (1) | AR006058A1 (enExample) |
| AT (1) | ATE212332T1 (enExample) |
| AU (1) | AU725472B2 (enExample) |
| BG (1) | BG63664B1 (enExample) |
| BR (1) | BR9707811A (enExample) |
| CZ (1) | CZ293415B6 (enExample) |
| DE (1) | DE69710052T2 (enExample) |
| DK (1) | DK0888291T3 (enExample) |
| EA (1) | EA000955B1 (enExample) |
| ES (1) | ES2166977T3 (enExample) |
| GB (1) | GB9604691D0 (enExample) |
| HR (1) | HRP970128B1 (enExample) |
| HU (1) | HU228635B1 (enExample) |
| ID (1) | ID17221A (enExample) |
| IL (1) | IL126054A (enExample) |
| IN (1) | IN186421B (enExample) |
| MY (1) | MY116862A (enExample) |
| NZ (1) | NZ331670A (enExample) |
| PL (1) | PL187340B1 (enExample) |
| PT (1) | PT888291E (enExample) |
| RO (1) | RO118534B1 (enExample) |
| RS (1) | RS49587B (enExample) |
| TR (1) | TR199801751T2 (enExample) |
| TW (1) | TW574185B (enExample) |
| UA (1) | UA57729C2 (enExample) |
| WO (1) | WO1997032843A1 (enExample) |
| ZA (1) | ZA971855B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110981806A (zh) * | 2019-12-06 | 2020-04-10 | 江苏优普生物化学科技股份有限公司 | 合成芳基吡唑腈副产碳酸二酯的方法 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1103759C (zh) * | 1997-03-03 | 2003-03-26 | 罗纳-普朗克农业公司 | 杀虫剂中间体的制备方法 |
| EP0952145B1 (en) * | 1998-04-20 | 2005-10-05 | BASF Agro B.V., Arnhem (NL), Wädenswil-Branch | Process for preparing pesticidal intermediates |
| ID27569A (id) | 1998-04-20 | 2001-04-12 | Aventis Agriculture Ltd | Proses-proses untuk membuat bahan-bahan pembunuh hama |
| EP0952144B1 (en) * | 1998-04-20 | 2003-06-18 | Bayer Agriculture Limited | Processes for preparing pesticidal intermediates |
| FR2789387B1 (fr) * | 1999-02-04 | 2001-09-14 | Aventis Cropscience Sa | Nouveau procede de preparation d'intermediaires pesticides |
| EP1264823A1 (en) * | 2001-06-08 | 2002-12-11 | Novartis AG | Process for the preparation of 2,3-dicyanopropionates |
| DE10142665B4 (de) | 2001-08-31 | 2004-05-06 | Aventis Pharma Deutschland Gmbh | C2-Disubstituierte Indan-1-one und ihre Derivate |
| WO2005023773A1 (en) * | 2003-09-04 | 2005-03-17 | Pfizer Limited | Process for the preparation of substituted aryl pyrazoles |
| GB0414890D0 (en) * | 2004-07-02 | 2004-08-04 | Pfizer Ltd | Process for preparing synthetic intermediates useful in preparing pyrazole compounds |
| CN100391936C (zh) * | 2005-11-07 | 2008-06-04 | 栾忠岳 | 一种合成2、3-二氰基丙酸乙酯的工艺 |
| ES2433427T3 (es) * | 2009-03-16 | 2013-12-11 | Merial Limited | Proceso para la preparación de derivados de pirazol |
| AU2010100309A4 (en) * | 2010-01-18 | 2010-05-20 | Keki Hormusji Gharda | A process for the preparation of cyanoalkylpropionate derivatives |
| WO2012147093A1 (en) | 2011-04-25 | 2012-11-01 | Keki Hormusji Gharda | A process for preparation of dicyanocarboxylate derivatives |
| CN103214395B (zh) * | 2013-03-26 | 2014-04-30 | 南通市海圣药业有限公司 | 2,3-二氰基丙酸乙酯的合成工艺 |
| CN106117145A (zh) * | 2016-07-12 | 2016-11-16 | 潍坊鑫诺化工有限公司 | 5‑氨基‑1‑（2,6‑二氯‑4‑三氟甲基苯基）‑3‑氰基吡唑的制备方法 |
| CN113372240A (zh) * | 2021-07-02 | 2021-09-10 | 湖北金玉兰医药科技有限公司 | 一种2,3-二氰基丙酸乙酯的绿色制备工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8531485D0 (en) * | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
| US5232940A (en) * | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| GB9120641D0 (en) * | 1991-09-27 | 1991-11-06 | Ici Plc | Heterocyclic compounds |
| GB9306184D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
-
1996
- 1996-03-05 GB GBGB9604691.7A patent/GB9604691D0/en active Pending
-
1997
- 1997-03-03 BR BR9707811A patent/BR9707811A/pt not_active IP Right Cessation
- 1997-03-03 DK DK97907063T patent/DK0888291T3/da active
- 1997-03-03 PT PT97907063T patent/PT888291E/pt unknown
- 1997-03-03 CZ CZ19982809A patent/CZ293415B6/cs not_active IP Right Cessation
- 1997-03-03 DE DE69710052T patent/DE69710052T2/de not_active Expired - Lifetime
- 1997-03-03 AU AU19248/97A patent/AU725472B2/en not_active Ceased
- 1997-03-03 NZ NZ331670A patent/NZ331670A/en not_active IP Right Cessation
- 1997-03-03 AR ARP970100828A patent/AR006058A1/es active IP Right Grant
- 1997-03-03 CN CNA031522416A patent/CN1495168A/zh active Pending
- 1997-03-03 PL PL97328778A patent/PL187340B1/pl unknown
- 1997-03-03 JP JP53143797A patent/JP4039693B2/ja not_active Expired - Lifetime
- 1997-03-03 CN CNB971928673A patent/CN1137090C/zh not_active Expired - Lifetime
- 1997-03-03 IL IL12605497A patent/IL126054A/xx not_active IP Right Cessation
- 1997-03-03 HU HU9902473A patent/HU228635B1/hu unknown
- 1997-03-03 US US09/142,074 patent/US6133432A/en not_active Expired - Lifetime
- 1997-03-03 KR KR1019980706867A patent/KR100530974B1/ko not_active Expired - Lifetime
- 1997-03-03 AT AT97907063T patent/ATE212332T1/de not_active IP Right Cessation
- 1997-03-03 RO RO98-01349A patent/RO118534B1/ro unknown
- 1997-03-03 WO PCT/EP1997/001036 patent/WO1997032843A1/en not_active Ceased
- 1997-03-03 EP EP97907063A patent/EP0888291B1/en not_active Expired - Lifetime
- 1997-03-03 UA UA98095184A patent/UA57729C2/uk unknown
- 1997-03-03 ES ES97907063T patent/ES2166977T3/es not_active Expired - Lifetime
- 1997-03-03 EA EA199800792A patent/EA000955B1/ru not_active IP Right Cessation
- 1997-03-03 ID IDP970644A patent/ID17221A/id unknown
- 1997-03-03 TR TR1998/01751T patent/TR199801751T2/xx unknown
- 1997-03-04 ZA ZA9701855A patent/ZA971855B/xx unknown
- 1997-03-04 MY MYPI97000874A patent/MY116862A/en unknown
- 1997-03-04 HR HR970128A patent/HRP970128B1/xx not_active IP Right Cessation
- 1997-03-04 IN IN556DE1997 patent/IN186421B/en unknown
- 1997-03-07 TW TW086102820A patent/TW574185B/zh not_active IP Right Cessation
-
1998
- 1998-09-04 RS YUP-387/98A patent/RS49587B/sr unknown
- 1998-09-24 BG BG102788A patent/BG63664B1/bg unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110981806A (zh) * | 2019-12-06 | 2020-04-10 | 江苏优普生物化学科技股份有限公司 | 合成芳基吡唑腈副产碳酸二酯的方法 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1213366A (zh) | 制备杀虫剂中间体的新方法 | |
| CN107963996B (zh) | 一锅法制备3-三氟甲基异噁唑化合物的方法 | |
| CN106660928A (zh) | 用于制备(e,z)‑7,9‑十二碳二烯基‑1‑乙酸酯的新方法 | |
| US4228299A (en) | Chemical process for preparing alkyl esters or the amide of 3-(β,.beta. | |
| EP1735262A1 (en) | Process for preparing cinnamic acids and alkyl esters thereof | |
| KR20220039116A (ko) | 고순도 펠루비프로펜의 제조방법 | |
| JP2000169425A (ja) | ２―アルキル―３―ヒドロキシ安息香酸の製造方法 | |
| US4767880A (en) | Process for racemizing optically active alpha-phenoxypropionic acid and derivatives thereof | |
| CN1157358C (zh) | 一种合成2,2-二甲基-3-(1-丙烯基)环丙烷羧酸酯的方法 | |
| EP1940770B1 (fr) | Nouveau procédé de préparation d'hydroxy-acides gras insaturés | |
| CA2257825C (en) | New processes for preparing pesticidal intermediates | |
| CN1040425C (zh) | 制备2-(2-甲基苯基)-3-甲氧基丙烯酸甲酯的化学方法 | |
| JP2000344723A (ja) | ニトリルの製造方法 | |
| JPH0142253B2 (enExample) | ||
| KR20060096427A (ko) | 1-[시아노(페닐)메틸]-사이클로헥사놀 화합물의 제조 방법 | |
| US4234506A (en) | Process for preparing cyanohydrin esters | |
| JPH11335329A (ja) | α−（アルコキシオキサリル）脂肪酸エステルおよびα−アルキルまたはアルケニルアクリル酸エステル類、およびそれを用いたフエニドン類の合成法 | |
| CN1043932A (zh) | 一种制备萘衍生物的方法 | |
| JP2965182B2 (ja) | β−ケトエステルの製法 | |
| JPH1059895A (ja) | マンデル酸誘導体の製造方法 | |
| MXPA98007125A (en) | New processes for the preparation of pesticide intermediaries | |
| Ashida | Development of Divergent and Parallel Synthetic Methods for (E)-and (Z)-Stereodefined Multi-Substituted Alkene Scaffolds | |
| CN1623973A (zh) | β－二酮酯的制备方法 | |
| JP2003261527A (ja) | α−アルキル−置換フェニルアセトニトリルの製造方法 | |
| JPS6011690B2 (ja) | 修酸誘導体およびその製法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |